(+)-(3-Bromopropyl)boronic Acid Pinanediol Ester

Base Information

• Chemical Name: (+)-(3-Bromopropyl)boronic Acid Pinanediol Ester
• CAS No.: 90084-37-0
• Molecular Formula: C₁₃H₂₂BBrO₂
• Molecular Weight: 301.031
• DSSTox Substance ID: DTXSID60451892
• Wikidata: Q82272181
• Mol file: 90084-37-0.mol

Synonyms:(+)-(3-Bromopropyl)boronic Acid Pinanediol Ester;90084-37-0;(1S,2S,6R,8S)-4-(3-bromopropyl)-2,9,9-trimethyl-3,5-dioxa-4-boratricyclo[6.1.1.02,6]decane;(3AS,4S,6S,7AR)-2-(3-BROMOPROPYL)-3A,5,5-TRIMETHYLHEXAHYDRO-4,6-METHANOBENZO[D][1,3,2]DIOXABOROLE;SCHEMBL8977537;DTXSID60451892;(3aS,4S,6S,7aR)-2-(3-Bromopropyl)-3a,5,5-trimethylhexahydro-2H-4,6-methano-1,3,2-benzodioxaborole

Chemical Property of (+)-(3-Bromopropyl)boronic Acid Pinanediol Ester

Chemical Property:

• PSA: 18.46000
• LogP: 3.49970
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 300.08962
• Heavy Atom Count: 17
• Complexity: 323

Purity/Quality:

(+)-(3-Bromopropyl)boronicAcidPinanediolEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B1(OC2CC3CC(C3(C)C)C2(O1)C)CCCBr
• Isomeric SMILES: B1(O[C@@H]2C[C@@H]3C[C@H]([C@@]2(O1)C)C3(C)C)CCCBr
• Uses: As a pinanediol boronic ester derivative, (+)-(3-BroMopropyl)boronic Acid Pinanediol Ester can be used in the preparation of thrombin inhibitors.

Technology Process of (+)-(3-Bromopropyl)boronic Acid Pinanediol Ester

There total 6 articles about (+)-(3-Bromopropyl)boronic Acid Pinanediol Ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 80.0%

trimethylsilan (993-07-7) + pinanediol (18680-27-8) + boron trichloride (10294-34-5) + allyl bromide (106-95-6) → (3aS,4S,6S,7aR)-2-(3-bromopropyl)-3a,5,5-trimethylhexahydro-4,6-methanobenzo[d][1,3,2]dioxaborole (90084-37-0)

Guidance literature:

In diethyl ether; Ar-atmosphere; addn. of Me3SiH and allyl-Br to BCl3 at -78°C, evapn., cooling (ice bath), addn. of Et2O soln. of pinanediol, stirring for10 min; collection (distillation, 145°C/0.25 Torr); NMR spectroscopy;

DOI:10.1021/om00009a018

Reference yield: 73.0%

pinanediol (18680-27-8) + 2-(3-Bromopropyl)-1,3,2-benzodioxaborole (90084-34-7) → (3aS,4S,6S,7aR)-2-(3-bromopropyl)-3a,5,5-trimethylhexahydro-4,6-methanobenzo[d][1,3,2]dioxaborole (90084-37-0)

Guidance literature:

In tetrahydrofuran; Equivalent amounts of reagents were mixed in THF;; concn., chromy. on silica gel with ether-hexane, distillation; elem. anal.;;

Reference yield: 64.0%

pinanediol (18680-27-8) + allyl bromide (106-95-6) + benzo[1,3,2]dioxaborole (274-07-7) → (3aS,4S,6S,7aR)-2-(3-bromopropyl)-3a,5,5-trimethylhexahydro-4,6-methanobenzo[d][1,3,2]dioxaborole (90084-37-0)

Guidance literature:

allyl bromide; benzo[1,3,2]dioxaborole; at 100 ℃; for 3h; Inert atmosphere;

pinanediol; In tetrahydrofuran; at 0 - 20 ℃; Inert atmosphere;

DOI:10.1021/acs.jmedchem.6b01021

upstream raw materials:

pinanediol

2-hydroxy-1,3,2-benzodioxaborole

allyl bromide

(+)-α-pinene

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